Small Business Tax Savings Podcast
Oct 7, 2026 · 24 min · 10 segments
Your health insurance could do more than cover medical emergencies. With the right strategy, it could also help you save on taxes. In this episode, Mike Jesowshek, CPA, breaks down health insurance…
So when we're looking to offer plans and offer a health insurance item, we have to start to look at what options are available out there.
And typically, I'm gonna say if you have employees that you want to offer a health insurance plan for, what we're looking at are group plans.
You could look at an HRA, whether that's a QSEHRA, an ICHRA, something like that.
You could do a stipend, where they'll just say, "Hey, we're just gonna pay you more, and it's gonna be taxable to you, but we're gonna pay you more." Or another option is just do nothing.
You have to go figure out health insurance on your own." So let's look about, again, at those options: group plan, self or level funded, an HRA, a stipend, or just do nothing at all.
That's what I really look at when we look at what do we offer for health benefits for employees.
And then we also need to look at the treatment for an employee versus just self-employed.
So if you're just self-employed, the payments that you make for health insurance, you can go on the marketplace, you can get your plan wherever you want to get your plan.
And we might look at a different type of option or plan for those that are just self-employed versus what we're gonna offer our employees.
So if you have employees, we're definitely gonna look at a whole kind of what does the whole picture look like.
If you don't have employees, then the only thing that we're looking to serve is you, and so we need to look at what do we want to offer for health insurance.
When I started my business, this is exactly where I didn't know what to go down this route, and I just got scared, and like, "I don't know what I'm gonna offer for health insurance.
All I know is that health insurance is expensive, and if I start to offer it, it's probably gonna cripple my business." But what I have found as I've grown in, into the tax strategy piece and as I've grown as a business owner, there are really good options out there.
You just need to know what options they are, and we're gonna dig a little bit deeper into that a little bit later.
So when we're looking to offer plans and offer a health insurance item, we have to start to look at what options are available out there.
And typically, I'm gonna say if you have employees that you want to offer a health insurance plan for, what we're looking at are group plans.
You could look at an HRA, whether that's a QSEHRA, an ICHRA, something like that.
You could do a stipend, where they'll just say, "Hey, we're just gonna pay you more, and it's gonna be taxable to you, but we're gonna pay you more." Or another option is just do nothing.
You have to go figure out health insurance on your own." So let's look about, again, at those options: group plan, self or level funded, an HRA, a stipend, or just do nothing at all.
That's what I really look at when we look at what do we offer for health benefits for employees.
And then we also need to look at the treatment for an employee versus just self-employed.
So if you're just self-employed, the payments that you make for health insurance, you can go on the marketplace, you can get your plan wherever you want to get your plan.
And we might look at a different type of option or plan for those that are just self-employed versus what we're gonna offer our employees.
So if you have employees, we're definitely gonna look at a whole kind of what does the whole picture look like.
If you don't have employees, then the only thing that we're looking to serve is you, and so we need to look at what do we want to offer for health insurance.
When I started my business, this is exactly where I didn't know what to go down this route, and I just got scared, and like, "I don't know what I'm gonna offer for health insurance.
All I know is that health insurance is expensive, and if I start to offer it, it's probably gonna cripple my business." But what I have found as I've grown in, into the tax strategy piece and as I've grown as a business owner, there are really good options out there.
You just need to know what options they are, and we're gonna dig a little bit deeper into that a little bit later.
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